How i work

I’m Cyrus Massoumi, Founder and CEO of ZocDoc, and This Is How I Work

Tessa Miller

Finding a good doctor can feel like finding a needle in a haystack. So many factors are involved in the search: location, medical specialties, accepted insurance, bedside manner, etc. Even after you select a doctor to see, it can take days and sometimes weeks to get an appointment. ZocDoc CEO Cyrus Massoumi is changing that.
As he sees it, healthcare should be reviewed and booked online just as easily as restaurants and travel. Launched in 2007,
ZocDoc allows users to narrow down their doctor and dentist search using a variety of criteria, read patient reviews, book appointments, and even fill out necessary paperwork pre-visit. Best of all, most users receive medical care in less than 72 hours. We caught up with Cyrus to chat about what inspires him, the tools that keep him organized, and how he gets through airports at lightening speed.
Current gig: Founder and CEO, ZocDoc
Location: New York, NY
Current mobile device: iPhone 5
Current computer: I'm a PC guy at work, a Mac guy at home
One word that best describes how you work: Plan. Every minute of my day is planned.

What's apps/software/tools can't you live without?

I have a pretty awful sense of direction, so I couldn't live without my mobile maps. Out of my friends, I'm one of the few who uses Apple Maps, but I actually really like it. It's fast and it shows building outlines plus shortcuts on certain blocks in NYC, which I appreciate. I use Siri every day to set my alarm for the following morning. The Kindle app is great because it allows me to catch up on my reading here and there, even if I don't have my actual Kindle with me. Also, at ZocDoc, we essentially live by our calendars. We're all pretty religious about it—from sending calendar invitations, to scheduling our travel and vacations or even for booking conference rooms for meetings. It helps keep us all on the same page.

What's your workspace set up like?

I sit in an open cubicle and decorate it with fun gear. The top of my cube is lined with a bunch of ZocDoc-branded converse sneakers, a ZocDoc hard hat, and a ZocDoc shoe bin—the kind you see at airport security. I also have a double monitor set up there, and I tend to use one monitor for easy access to my database of contacts and the other monitor for everything else. My cubicle sits under a big sign that says "Make Work Fun" which is one of our seven core values here. As far as my workspace is concerned, I aim to keep my desk immaculate. I don't think you can effectively lead if your desk is a mess.

Pictured above: Cyrus' desk.

What do you listen to while you work?

I like to keep my ears open while at work. It's amazing how much you can learn in passing about people, projects, teams and new ideas. Also, we encourage everyone at ZocDoc to "Speak Up" (another core value here), and I think they'll be less inclined to approach me if I have my ears plugged. If there's a time that I really need to hunker down at my desk, block everything out, and focus, I'll listen to Pandora. It's been on the Sia station for over a year and I haven't gotten around to changing it—so Sia has become my default focus music.

What's your best time-saving trick?

I shave less frequently—to me, a little scruff is worth the time saved. Also, we're growing so quickly that I spend a ton of my time these days interviewing candidates. I try to keep these interviews to just 15 minutes, and I have gotten good at screening for a few important characteristics. This helps me and the company save time, and it keep our hiring process humming along. I've also started creating a weekly pie chart, outlining how I'd ideally like to spend my time that week. It's a good way of holding myself accountable for how I'm allocating my time, and this structure helps me tackle on items that need my immediate attention, while also setting aside time to plan and strategize for the future.

What's your favorite to-do list manager?

My email inbox. The only emails I keep in there are things I need to do. My daily goal is to eliminate the scrollbar on my inbox and delete anything that doesn't require an action.

Besides your phone and computer, what gadget can't you live without?

I'm working on carrying less stuff around, so I'm trying to streamline as many functions as possible through my phone to lighten my load. I do love my Livescribe pen, though. I use it in all of my meetings.

Pictured above: Cyrus' Livescribe pen.

What everyday thing are you better at than anyone else?

I'm pretty skilled at getting through an airport at lightning speed, and I sort of make a personal game out of it—like I'm playing Frogger, airport edition. I'm a huge fan of all of those pre-security clearances like the TSA Pre-Check and CLEAR, which help get you through security much faster and don't require you to take off your shoes, belt, etc. When I'm travelling with colleagues, they joke that we basically race through the airport.

What's your sleep routine like?

I'm a night owl. I sleep about 5-6 hours a night and tend to go to bed fairly late. I need everyone else to go to sleep so my emails stop coming in, and late at night is when I make the most headway on getting rid of that inbox scrollbar.

Are you more of an introvert or an extrovert?

I think I'm the textbook definition of an extrovert. I am energized when I'm surrounded by the team at ZocDoc, my friends, and my family. I love meeting new people, and I have no hesitation when it comes to striking up conversations. I also don't think it'd be physically possible for me to be an introvert, because—as everyone at the office can attest—I'm a walking megaphone. My voice is naturally incredibly loud (so loud, in fact, that I can hail a cab from a block away).

Fill in the blank: I'd kill to see _________ answer these same questions.

I'd have to say Steve Jobs, when he was simultaneously CEO of both Apple and Pixar. It's hard enough to be the CEO of just one company.

What's the best advice you've ever received?

Never give up